Forced To Cross Dress Stories
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Forced To Cross Dress Stories
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Screwed the Bet, Forced to Cross Dress
Hi, um… I have a small problem. My name is Tom. I’m 18 and I, um, made a bet that the Michigan Wolverines were going to beat the Tennessee Volunteers in football.
Well, it got out of hand and I either pay $250 all around or live like a woman for a week- panties, bra, makeup… the whole thing. I don’t have $500 so I’ll go with the woman thing. I need advice. I’m not asking friends because I want to keep it between us three guys. Please help me. – Dragged to Drag (Franklin, TN)
Sweetness, there are two things you must keep in mind:
1) The only sure thing is that most bets have a 50-50 chance of losing . If you are not prepared to be on the wrong side, don’t bet in the first place. 2) There’s nothing uglier than a macho man dressed in drag.
The only advice I have is find a sister, best girl, or any other female with a sense of humor and borrow some clothes. No one said you need to look like a femme fatal – jeans and a t-shirt, some lipstick, and goop in your hair will suffice. Any tranny will tell you that Payless goes all the way up to a size 13 in women’s shoes… find something you can walk in!
Then it’s your decision to either stay in the house all week and watch daytime TV where you can listen to more fools in a similar predicament to yours or go out and have fun with it! At least you’ll have a zany story to tell your kids down the road.
Hope you’re not pulling my leg with this email, or I’ll have to tell my local she-male, Helga and the Angry Twelve Inch.
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5 pages February 14, 2016 London Rose
Alex fey is in a mess thanks to her wonderful parents . Will she accept her fate or run away ?
17 pages Completed March 22, 2013 BlackRose
"You will marry me and that is final!" he yelled at her.
"I will never marry you! Not now or never! I don't love you!"
"Oh we will see about that."
16 pages Completed June 3, 2015 The Ginger Ninja
An interesting story where a boys cross dressing habit snowballs. The pic is Julie/John.
2 pages June 25, 2013 Prince of Kawaii
A story about a young male and his crossdressing adventures.
Inspired by Udagawachou de Mattete yo.
2 pages December 28, 2012 Saxon Dog
What if zombies are not mindless? What if they still retain the mind of who they once were? Maybe they are trapped by something evil that controls them. Maybe they are searching for help. Maybe a zombies moan isn't one of hunger. Maybe its a cry for help.
This is a new story involving detectives and comedy and set in England, 1886... Well to be honest i'm not that good at comedy so just like pretend it's funny! (*=v=*) By S.C.Bach
12 pages Completed December 3, 2012 B. M. P
The story of a forced utopian society
22 pages Completed March 11, 2014 Stephanie
Games will be played, trouble will occur, and death will be consistent...
3 pages August 28, 2017 Noodle Alien.anon
Join Elliot in an unusual encounter.
3 pages Completed April 6, 2021 Savanah Autman
John befriends Clark, a young teenaged boy who likes crossdressing but is afraid to tell his dad due to his traditional beliefs of young men who are supposed to be masculine. With the help of the angels, he will see to it that anyone such as him can be themselves within their own skin.
2 pages May 10, 2017 Josh liak
When my best friend Kai gave up his life he left notes for 5 people to sum up who it was that made him commit suicide. Follow my journey to find out which person really forced him to take his life.
12 pages July 10, 2018 Ronaween Vitug
Riz Vanz Ludwig had no other choice but to pretend that she's her twin brother, Rez Vince. Pretending to be a guy all for the sake of Basketball is not an easy task. Then, she meets Alexander Marco, Rez's roommate and friend who's also the team captain of the Basketball team.
How will Ri...
5 pages Completed March 26, 2016 Turnoffthelightsbabe
She adored dancing, yet they forced her to dance too long, they kicked her shins and expected her to not waver as she continued to twirl, her hobby became the noose around her neck, and they tightened it.
(Heavy flower symbolism. But meanings will be at the end of the chapter. This is a gist of my l...
2 pages March 27, 2014 Cameron Riley
Eva kept a journal all through childhood. When she is forced into a rehabilitation center, she is forced to keep a journal. Why would Makarov let such a thing happen to his little sister?
47 pages Completed March 31, 2013 Arabella-Jane
Things have changed since before. Poor families are forced to sell off their daughters to rich men like pieces of property.
I'm one of those daughters.
I've been terrified of what abuse I would be forced into, until I met a boy who resists society. It was then that things spiraled out of c...
6 pages February 17, 2013 Adriana
There are things in life we can't really explain or begin to understand. For example, why my dad doesn't ever call or talk to me, or why we're forced to go to school. When Andie moves and has to completely start over, her life is turned upside down, and she's forced to face challenge...
Bailey Hanson. A sophomore in high school and a member of the Drama and Tree-Huggers Clubs. She liked to consider her life an easy-going one, never forced to experience hardships, unless you consider finals a hardship. She has many acquaintances but few friends, mainly because she likes to keep to h...
9 pages Completed March 4, 2013 Just another guy
Josh was kidnapped and forced to fight all manner of people to the death...
3 pages September 18, 2013 Vulcan Mortician
Here are some vignettes I was forced to write in summer school.
3 pages March 14, 2014 Stephanie
“I dare you to put him in dresses. You are afraid to admit he is more of a wife than the husband.” “You…
I had to be crazy! I’m supposed to be a normal teenage boy lusting after pretty girls yet more and more I was…
For a long time it was absolute magic, a beautiful broken taboo blooming with fantasy where…
“I like to wear women’s clothes and I need to wear them”, that is how I became a wife of a crossdresser…
Not coming out, we often lie to our wives and the very people with whom we should be the most honest.
These were the top 10 stories tagged with Crossdressing in 2021. You can also dive into monthly archives for 2021 by using the calendar at the top of this page.
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I arrived home, from work, on the Bank Holiday weekend, of Easter. The following week, I was taking days off that were owing to me, so the forecasts were good, and I was happy. As I entered the house, I heard chatter, and recognized my mom and aunt Marilyn’s voice.
“Hello son, look who is here.” mom spoke, as I gazed at aunt Marilyn. I had always and still am, very fond of her, and fantasized about her, when in bed and in the shower. I know it is wrong, I told myself, but that was my secret.
Mom: “Aunt Marilyn, is here, to ask you, if you would like to spend some of your days off work, at her home.”
Me: “Yes, I will accept the offer mom, and thank you aunt Marilyn.”
Well we sat down to a meal and my aunt slept over that night, so we made an early start in the morning.
Aunt Marilyn: “Did you sleep well Graham, as we got into the car?”
Me: “Not really aunt, as I was excited about this stay with you. ”
I waved my mom goodbye. The journey took us about ninety minutes, and arrived in Park Close, a cul-de-sac, with six bungalows there. It was a tranquil area, and in the countryside. I liked the closed in hedges of the lanes, we drove down, were beyond the hedges, laid open fields of grass and crops.
My valise case (a small travelling bag), just carried my bathroom kit, a few underpants and tops, a pair of blue jeans, a white ladies blouse, full sleeves with a Peter Pan collar, a pair of white knickers and ladies beige slacks, with a button and zip, side fastening.
Aunt Marilyn, showed me around and where everything was. Then we left, to go for fish and chips, to eat at Tally’s. On return, aunt took a shower, and offered me to take one after her, which I did, to freshen up.
About an hour later, aunt, telling me, as I was reading a woman’s magazine of hers, that she just be over the road, to chat to her friend for awhile.
Me: “ Yes aunt, go ahead, is it okay if I do this crossword aunt?”
Aunt Marilyn: Yes sweetie make yourself at home.
I was still with a bath towel around my waist, male sarong style, not female, with it covering my bust.
Once aunt left, I had the urge to peek into her boudoir, and there on the bed, was a lovely shade of pink, nightdress. Oh gosh, as I stared at it, but dared not touch it, in case aunt had placed it, in a certain way. Weakness of a man overcame me, and I found myself holding it up in front of me, then dropping the towel, to the carpet, and stood in front of the mirror, and with a rampant erection, as I had not mastur-bated for about five days. Oh gosh, as I was now mesmerized, then it touched the top of my pe-nis. Oh no, as I hoped my precum had not stained it.
Then to my horror, my aunt’s voice at the door, saying, ” if you like it so much, why not put it on.”
Me: “ I can explain aunt Marilyn. Please don’t tell my mom.”
Aunt entered the room, locked the door, and came toward me.
Aunt Marilyn: Now my teenage niece, we best get you into your nightdress, and early for bed.
Taking the nightie from me, slipped it over my head, not mentioning my arousal.
Aunt Marilyn: “Pink, does become you, Jane, Very cute indeed. You shall wear it tonight and if you make a mess in it, you will hand wash it, and you will wear another one of my nighties, each night, until you leave. You see Graham, I mean Jane, as I unpacked your valise earlier, I noticed a certain few items, that only could belong to a girl wearing them, so to confirm it, made an excuse to leave you alone for awhile, to discover you, in a compromising position, which I have done. Now my sweet young niece, we best go and watch the film on DVD, ” THE WOMEN.” Tomorrow morning, you shall wear what I put on my bed for you. Any argument or protest, then your mom will be contacted. Do you understand Jane?”
Aunt Marilyn: “ Now, when you need to use the bathroom, you will sit down to pee. You are now my niece, a girl. We are going to have such fun, while you are here. Oh you’re going to see some change in you. ”
I sensed my boyhood, being overtaken by a new ultra-feminine existence, while at aunt Marilyn’s.
What a wonderful way to get caught.
Lovely story, could use some sharpening up concerning your writing grammar but I did love it. We all want an aunty like that, to be told what to do to bring our feminine side out. Kisses hon.
Beverly
had a similiar experience ,but my aunt had a strapon that she used very well it vibrated on her pussy as she laid the wood to me felt great.
Could of been oh so much better and longer.
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